


A Second Chance Side Story - Retry

by ChibiEdo



Series: A Second Chance [2]
Category: Homestuck
Genre: 2 Dirks, 2 Jakes, ASC AU, Alternate Universe - No Sburb Session, Anal Sex, Established Relationship, Fluff, Illustrated, M/M
Language: English
Status: Completed
Published: 2014-02-14
Updated: 2014-02-14
Packaged: 2018-01-12 07:06:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,656
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1183334
Author URL: https://archiveofourown.org/users/ChibiEdo/pseuds/ChibiEdo
Summary: <blockquote class="userstuff">
              <p>This is a little sidestory based on my "A Second Chance" comic (which I also have here on archive).<br/>It's basically fluffy porn and Jakes being, well Jakes. Yes, plural.</p>
            </blockquote>





	A Second Chance Side Story - Retry

**Author's Note:**

> First of all, this is my first piece of writing ever so I'd really appreciate some feedback. I really like how it turned out so I hope you will enjoy the read!  
> Thanks a lot for LateNiteSlacker for beta-ing. If you see weird sentence structures chances are high I left them in there intentionally, so don't blame her for that.XD
> 
> A bit more info: Timeline wise it takes place close to the end of the main story. Currently the comic hasn't even reached past-Dirk yet so I put in some information throughout this oneshot to hopefully make you less confused.

Your name is Dirk Strider and you are currently looking at one of the most beautiful things in the world.  
It consists of a thin rectangular surface, called a flat screen, which is in turn connected to an electricity powered plastic box, called a computer. Which you are dead-set on taking apart eventually to figure out its inner workings. But not right now. Because at the moment the screen is displaying lines of black text on a white background.

Code.

You never knew what you had missed out on until you were graced with the knowledge of the existence of programming languages and what they were capable of.

Speeding up mathematical procedures. Automating a variety of specific tasks. Solving a plethora of problems. Controlling the behavior of robots. Creating Artificial Intelligence.

The possibilities are endless and right at your fingertips. You just have to know how to utilize them.  
It is truly mind-boggling.

But before you can devote yourself to the more fascinating application of code you have to learn the basics of data structures. Luckily the one teaching you is none other than Dirk Strider, who happens to be an expert on robotics and AI.

And yes that is indeed his name. Matching your own. Your names are not the only similarity. You hate to admit it, but there is a great resemblance between you and him. Facial features for example. Pale skin and orange irises. Which he tends to hide under those ridiculous triangular shades of his. He is not wearing them right now though. Both of you are blond, but while your short hair is more on the pale side, his is more golden, marginally longer and unnaturally spiked upwards. That gent clearly spends too much time on utterly pointless tasks, but you digress.

You might want to add that you would technically be his great-great-great-uncle.

This can be easily explained, considering the fact that you are currently in a time period that isn't your own. Presently the year is 2013, but that's not the year you live in. You are from 1922, and you ended up here by time traveling to save the person currently sitting next to you. The trip did not turn out entirely as planned, but you suppose that you did accomplish your goal. Now that you have finished what you came here to do, you believe you will eventually return to your own timeline. After spending some time here in the future.

Honestly, you don't really want to think about leaving yet. The current technology is more than fascinating and makes your mind reel.

Back to the task at hand. You are listening to Dirk explaining data structures and types with various examples. Variables, arrays, hash tables, trees, booleans, integers, characters, floats, strings. You absorb every ounce of information. The more you learn, the more you are itching to put your newfound knowledge to use. In fascination you stare at the screen while absentmindedly wondering why your lower back feels a little bit... off. As if... Wait, are you getting poked?

Startled, you turn your head in the direction of the offending touch to glare at whoever dares to poke you just to find none other than Jake English. Or rather two of them. The reason why two Jakes exist in the first place is a more complicated story you don't feel like elaborating on at the moment. On first glance people might think that they are twins. The same dark messy hair. The same black-rimmed glasses. The same bucktoothed smile. The same emerald eyes that always sparkle with an intensity upon finding something of interest. Yes, they might be hard to distinguish for the average person, but you can easily tell them apart. One being a bit taller and his face looking slightly more mature.

This is only natural, after all he is one year older than the other Jake. But especially... the way the older one of them looks at you. How his eyes light up when they see you. You know he loves you and knowing this makes your heart flutter inside your chest.

Usually.

Because right now your interest is fully focused on the screen in front of you and you are not quite pleased about any kind of interference.

Dirk seems to have acknowledged their existence too, looking at them with a slightly bemused expression.

You raise one eyebrow at the Jakes. "What is it?" you ask, not hiding the slight annoyance seeping into your words.

Completely ignoring your tone of voice, your Jake wraps his arms around you from behind. "What are you doing, mate?"

"Learning about data structures," you reply, not bothering to sound very friendly.

Jake pulls a face at you. "Doesn't sound that exhilarating. Can't we all indulge in some kind of activity together? We're bored." To accent this he points towards the other Jake who has an equal expression of utter boredom on his face. Your only retort is another glare. Can't they see you are busy? You do not want to be disturbed, is this so hard to understand?

Dirk chuckles lightly. Apparently he doesn't seem to mind the interruption as much as you do. He slowly shakes his head. "Why don't you do something with just the two of you?" he suggests.

The other Jake's face lights up. "Was that an ok to screw the other me?"

Wait, what? Jakes really come to the weirdest conclusions sometimes. You really don't comprehend how their minds function. You tried to, but eventually gave up. You sigh and decide not to comment on any of this.

"Sure why the fuck not. Technically it's more like some kind of esoteric form of masturbation when you guys are involved," Dirk smoothly replies in a nonchalant way.

You internally roll your eyes. You might not exactly agree with what he just stated but you don't have a problem with them getting intimate with each other. After all it wouldn't be the first time. Thinking back of the activities the four of you have already partaken in... yes, they could certainly classify as... highly interesting.

Suddenly you become aware of the fact that the two Jakes are eagerly staring at you. Silently waiting for your permission as well. So you force yourself to calm down from your displeased state and tell them that they are free to do whatever they want.

Upon hearing your reply the Jakes' faces split into equally large smiles. Then they share a knowing glance and begin to snicker. "We'll have a ripsnorter of a time, that's for sure!" your Jake declares sounding positively excited. Then he grabs the other Jake's hand and pulls him away. Assumably to the bedroom.

Ok, you honestly do not know what just took place with their... ominous snickering and all. You briefly wonder if you should be concerned, but more than anything you are glad that they are leaving you alone for now. Alone with the wondrous creation that is source code. You are very contented that this distraction named English is taken care of.

A few minutes later you are just beginning to grasp the beauty of arrays when you hear the shuffling of feet and someone sitting down on the couch. Which is also located in the room you are currently in. Did the Jakes just come back? Maybe they changed their mind. That certainly wouldn't be very surprising to you. Them being the most random people you ever met. But then you hear the sounds of kissing. They cannot possibly mean to... Your ears are swiftly graced with a very sexual moan definitely coming from one of the Jakes. Apparently they can.

With a defeated sigh you shift your gaze towards the center of the room. What you see stops your mind in its tracks for a brief moment. Both of the Jakes are making out on the couch. Naked. They are sitting on it with their feet touching the floor. Your Jake having his arm wrapped around the other while the other Jake is grabbing his shoulder in return. They are necking each other passionately and... touching each other's dicks. Feeling blood rushing to your lower regions, you cannot help but stare. You do not want to, but watching them is causing the beginnings of an erection. Which is a fact that is rather distracting and hard to ignore. Lying next to them, you also spy a bottle of lubrication. You are quite sure they are planning to do more than just touching. Displeased, you roll your eyes. This time it is not internally.

In the corner of your eye you notice Dirk's attention is fixed on the Jakes as well. His expression is slightly dazed. Eyes half lidded with brows furrowed in concentration. Slightly confused, your gaze travels down his arm. This easily answers the question that was beginning to form in your head. Dirk has one of his hands in his pants. Seriously? You raise an eyebrow at him.

One corner of his mouth turns up into a smirk. "Just enjoying the show," he states as if it's the most common reaction in the world. The fact that all three of them don't seem to have any sense of shame is still kind of mystifiying for you. You are not one to be easily embarrassed either, but this blatant display of sexuality is still something you are not entirely used to yet.

While you were absentminded for a moment, the Jakes had shifted their positions. Your Jake groaning in pleasure while the other one is licking his penis. Shortly after, he takes it completely into his mouth. Moving his head up and down. Sucking on it.

Ok, that's it. Any kind of productive thought processes are effectively eliminated from your mind. Your pants are getting uncomfortably tight. A faint blush beginning to color your cheeks from the heat you are starting to feel. Your mind is filling with sexual thoughts. Jake. You want to touch him. Want to make him gasp and moan and make him feel incredible. Want to kiss him until he can't form coherent thoughts anymore. Want to just show him how much you love him.

...Might as well give up on learning how to code for the day. You cannot concentrate anymore anyway. And since the one supposed to be teaching you is otherwise preoccupied as well... yes, let's focus on Jake instead.

You are definitely not the only one who came to this conclusion. "How about calling it a day? There are other things I'd like to do now. Like Jake," Dirk declares. Voice sounding husky from his apparent arousal.

Slowly shaking your head, a slight smile forms on your face. "I have to agree. It is quite uncomfortable to just be left in this state we are currently in. So let us do something about that."

Pushing yourself up from the chair, you think about your next actions. You wanted Jake. But you would prefer not to share him today. To have some privacy. Since you already have your mind set on something to do with him. Something he'll probably be overjoyed to participate in. So, you calmly walk towards the couch and stop in front of the Jakes. Who, unsurprisingly, don't seem to notice your presence. You audibly clear your throat. Immediately, they cease their activities and two pairs of green eyes settle on you.

"Excuse me good sirs, but I believe you have something that belongs to me. Something that is actually someone and happens to be my boyfriend," you politely request, finger pointing at the older Jake.

Both Jakes chuckle. Then your Jake flashes a smile at you. "Oh, I happen to be kind of busy right now, as you can clearly see."

"I am certainly aware of that fact, but you might want to consider coming over to the bedroom with me. Only you. Don't worry, I have no doubt the younger Jake will be entertained as well," you casually reply.  
Dirk had followed you while you had made your way to the couch. Standing behind it, he now reaches out to ruffle his boyfriend's hair who laughs in return. After taking note of the scene in front of him, it does not take long before the older Jake takes you up on your request.

"Righto! That sounds capital!" your Jake eagerly exclaims, facing you. Smiling at him, you link your fingers with his and pull him up. Trying to ignore Jake's hard-on. And how uncomfortable your pants are. You really cannot wait to get rid of them. Sooner rather than later.

Hand in hand you make your way to Dirk's guest room. Which is the room you are sharing with Jake during your stay in this century. Immediately, he crawls onto the bed and turns around to face you again. Looking at you expectantly.

Warmth begins to spread through your chest. Jake. He is yours and you are his and sometimes you can still hardly believe that he chose you of all people. You know that you are not exactly someone you would describe as "easy to get along with". With social skills being nearly nonexistant, you never managed to make friends easily. Nor did you actually want to. Because, to be honest, most people just bored you immensely. So why would you try to sacrifice any of your precious time for them?

Jake is special though. He is so different from anyone else you have ever met. His positive outlook on life. His excitement about random things. His willingness to put up with your antics. To support you with anything you do. His interest in your creations and your hobbies. Him being full of surprises.

His smile.

His eyes.

His face.

Just his everything is all rather endearing, and it just increases the love you feel for him. The fact that he is positively quite attractive as well is not exactly a bad thing either. Looking him directly into the eyes, you soften your gaze, a small smile on your lips.

Yes, you are going to make sure that today is a day he won't forget.

Swiftly you pull your shirt over your head and drop it to the floor. Then, you quickly unbutton your pants and pull them down. Your underwear and socks follow shortly after. During the process of undressing, you are aware of Jake watching you with considerable interest. You cannot say you dislike having his attention on you. You are not embarrassed either. Compared to Jake's slightly muscular body, yours seems skinny and frail, but it never really bothered you. After all, Jake evidently likes what he sees, judging by his twitching erection. On the other hand, you are not entirely unaffected either. Your penis continuing to stiffen from arousal as well.

After being completely devoid of clothes, you join Jake on the bed. Confidently, you reach out to softly cup his face with both of your hands, causing him to close his eyes and happily lean into your touch. Then, you tilt your head, allowing you to capture his lips with your own. Which you do. Closing your eyes as well, you lose yourself in the feeling of his mouth moving against yours. Contently, you smile into the kiss and wrap your arms around him to pull him closer. Forgetting everything around you for the duration of your kiss.

When you pull back a little you are looking straight into the face of a very delighted Jake. A faint blush dusting his cheeks. "So... would you happen to be interested in having butt sex with me?" he asks eagerly.

You cannot help but chuckle. Jake. Always so blunt. "Yes. Certainly interested," you reply. "Just let me get some lubrication first."

You open the drawer of the nightstand to retrieve the bottle of lubrication stored in it. Meanwhile Jake lies down on his back and watches you expectantly. Instead of doing anything which would match his anticipations though, you just place the small object into one of his hands. Causing his face to turn into a surprised frown. "I thought... uhm. Aren't you going to prepare me for this encounter? I quite prefer that over doing the deed myself... You aren't still cross with me from earlier, are you?" he stammers, sounding very confused.

Cross with him? So apparently Jake _did_ notice you being less than pleased for interrupting your computer studies. He only _chose_ to completely ignore that. Seems like he was not as oblivious as you thought he was. Obnoxious little fella. Have you mentioned already Jake surprises you sometimes? Not necessarily in a positive way.

Slightly miffed, you wordlessly raise an eyebrow at him. Your unconcealed annoyance makes Jake even more nervous, because he is looking at you guiltily, biting his lip. Waiting for a reply. Serves him right for having to be patient until he gets one.

Six seconds later, you decide that you shouldn't be doing this. Your expression softens again and you chuckle lightly. After all, you had already decided on making this special. Way to go Jake, managing to throw you off like that. Immediately, you focus on your initial plan again. Which is to make Jake extraordinarily happy today. By now he seems utterly confused by your behavior. Staring at you as if you went completely off the rocker. Not very surprising.

"I'd rather have you prepare me," you finally reply. A soft smile on your face.

Then you simply wait. Until Jake's mind begins to fully grasp what you just implied. His mouth is hanging slightly open in bewilderment while he keeps staring at you. It takes another couple of seconds before it hits him. "Wait, you don't say... you...? Oh my god, you can't possibly mean, you...!" he stumbles over his sentences, his voice becoming more and more agitated with every word. Realization dawning on him. Wide eyed, his face lights up like a halogen light bulb.

"Would you like to top?" you add. To make your intentions absolutely clear. In case Jake still had doubts about whether he had come to the correct conclusion or not.

"That would be absolutely capital!" Jake eagerly exclaims with the biggest smile. But shortly after, his expression falters again.

Wait, why he is he being unhappy now? This kind of reaction is not what you expected.

"Are you sure it will be ok? I... I don't want to hurt you, you know...," he says quietly, his voice trailing off.

Oh. Suddenly his behavior makes sense. Thinking back to the first time you tried to bottom - which was actually both of your first sexual encounters - you understand his concern. It had not exactly gone well. You lacking any kind of pain tolerance certainly did not help. Combined with the fact that you were extremely tight and definitely not prepared enough. And the fact that neither you nor Jake had any kind of sexual experience beforehand. And also the fact that you had not been able to get yourself to fully relax.

Both of you ended up switching places. But not before you had managed to calm Jake down. Who apparently felt incredibly guilty about having inflicted pain on you. Even though it was barely noticable after he had pulled out and he was clearly overreacting. It warms your heart though that he cares for you so much.

You have not tried again ever since. But that does not mean you were opposed to it, quite on the contrary. Jake and you kept practicing inserting increasing numbers of fingers over the span of multiple days to stretch your sphincter muscles. To prepare for the time you would finally be able to take the breadth of a penis.

You had decided you are ready now. Even though Jake still does not seem entirely convinved.

"Do not worry. My anus can accomodate four fingers now when it is stretched. I am sure that is quite enough," you assure him gently.

That statement causes Jake to just blink at you with a blank expression. But immediately after, he just bursts out into laughter. "Frig, Dirk! How can you even say things like that with a straight face?" he manages to force out between laughs.

His response causes you to frown slightly. You are not really sure what was so funny about your statement. It was the truth. Plain and unaltered. You shrug internally. As mentioned earlier: Fully understanding Jake is not a task you will accomplish anytime in the proximal future.

Deciding not to dwell on this any longer, you relax your expression again and lock eyes with him. Smiling gently. "So, what would you think about getting started?"

Jake's instantaneous reply is an enthusiastic nod. Beaming at you with excitement.

Comfortably you lay down on your back while Jake squeezes some of the lubrication onto one of his hands. Rubbing it between his fingers to warm it up to body temperature. You spread your legs and bend your knees. Placing your feet close to yourself to give Jake easy access to your rear.

Shortly after, you feel the familiar sensation of getting a digit pushed into you. You close your eyes, allowing yourself to relax and enjoy the feeling. It is not entirely sexual yet, but that does not mean you don't like it. Soon, a second finger is added. A light feeling of fuzziness is spreading inside your brain. Caused by the stimulation of the nerve endings located inside your anus. Yes, two fingers feel quite nice. Jake is moving them slowly.

In. And out. In. And out again.

Suddenly, a jolt of pleasure rushes through you. Followed by a low moan escaping your lips. You lazily open your eyes a fraction to look into Jake's forest green irises.

"May I ascertain that I managed to find your prostate?" Jake inquires, grinning at you. His face flushed from arousal. You suppose him touching and seeing you like this really turns him on. It would probably not be any different if your situations were reversed.

"Mmmh," you reply wordlessly, not bothering to utter a full sentence. Lost in sensation. Barely five seconds later you allow your eyes to close again.

He presses a third finger inside. It's tight, but not too tight. You concentrate on staying relaxed. It is getting harder to maintain a state of calmness though. With Jake brushing your prostate every other push. Eliciting more and more needy sounds from you.

You really do appreciate the fact that Jake is taking his time for this. Patience is not necessarily a trait you associate with him, so you are extra thankful. Right now you are the one growing impatient though. You are getting really aroused and you really want this. You really want _him_. _Now_.

"Jake..." you groan, your voice trailing off. "Could you please... now...? I think I am prepared well enough."

His eyes light up, and his smile grows even bigger. Gently, he pulls out his fingers, leaving you with a strange sensation of loss.

Before he continues with anything else, he crawls on top of you. Steadying himself with his forearms, he leans down to kiss you. You eagerly respond in kind. Wrapping your arms around him to pull him closer. The shift in movement causes his dick to brush against yours. Evoking a moan from both of you.

Soon after, Jake breaks the kiss. You can feel him trembling slightly. At the moment he is probably trying his best to hold himself back so as not to just start rutting against you. You are quite sure he would not last long.

"No need for any further delay. Come on, Jake. Just do it," you tell him with a gentle smile on your face. Your voice layered with huskiness. Glancing at him with half-lidded eyes.

You are really looking forward to the next part.

He gulps nervously, a noticable blush remaining on his face. Then, he moves backward again. Grabbing his penis to align it with your anal orifice. Afterwards, he looks at you with a questioning but eager expression. Waiting for permission. You really love your boyfriend. He can be so sweet sometimes.

You nod and he begins to push inside you. While he does so, you concentrate on keeping your breath steady and pushing out to open up your external sphincter. To facilitate entry. Relax. You tell yourself over and over.

Despite your efforts you start to get really strained. The head of Jake's penis feels bigger than you thought. What if your calculations were wrong? What if it does not fit? Just when you started to get worried if it will actually go in, you feel the glans passing both of your sphincter muscles, and suddenly, you feel so much better.

It does not hurt. It does not hurt! You quietly sigh in relief. Admitting to yourself that yes, you had been a little nervous as well. You have a strong aversion against pain after all.

"Still ok?" Jake asks with a dazed expression.

"Yes," you reply. Your voice almost a whisper. "Everything is fine. I honestly just want you to start moving. Very soon. So please stop asking, I assure you I will definitely inform you if you are causing me any kind of discomfort."

Happy with that response, Jake smiles and pushes the rest of his dick inside you. It easily slides in. Slowly, he starts moving. Lazy thrusts that gradually increase in frequency.

The lightheaded feeling in your mind is back. And the intense sensation of arousal everytime his penis makes contact with your prostate. He leans over you again. Giving you the ability to put your arms around him. You feel so close. But you want to have him even closer. As close as you can possibly get.

You cling to Jake as if he's your lifeline. Arms tightly wrapped around him while he is rhythmically moving in and out of you. His breathing is getting more ragged from the exertion. And then he uses one hand to grab your penis. Moving it in sync with his thrusts.

It does not take long before you are completely undone. Moaning his name. Getting enveloped in the heat. You are writhing and shaking. You gasp everytime he manages to hit that certain spot inside you that makes you see stars. Your mind is drawing a total blank. Because this is intense! You are assaulted by sensations you never felt like this before. And it feels so incredible. Suddenly, everything just. Stops. You feel your orgasm wracking through you as you ejaculate. Semen splaying across your chest. Panting heavilly.

Still dizzy, you sense Jake release around seventeen seconds after you. Coating your insides with his sperm. He stills all movement and waits until the last wave of his orgasm subsides before he eventually pulls out. Then he lays down beside you and cuddles into you, wrapping his arms around you. You immediately return the gesture. Because there is nothing you would like to do more in the current moment.

"Holy dickens, that was exhilarating!" Jake exclaims with a look of excitement and happiness on his face.

"Yes. Yes it was," you respond. Feeling peaceful and ecstatic at the same time. Words cannot quite describe how you feel right now. But you have never felt better.

"I love you so much, Dirk," Jake mumbles quietly. Closing his eyes and tightening his hold on you.

Your heart always beats faster when you hear him say that. You can never get enough of this. All this. His love. Him having sex with you.

"I love you too, Jake," you softly reply. Leaning your head into the crook of his neck. Smiling brightly.

Your chest is a mess, with your semen smeared across you and Jake by now, but neither of you can bring yourself to care. Very soon, you both fall into a peaceful slumber. Safe and content in each other's arms.


End file.
